Imidazole → HCID 58944550, compound

HRID 222182Notes

Reaction equation

HRID 222182 reaction equation
[NH2:1][C:2]1[C:3]2[CH:10]=[CH:9][N:8]([C@H:11]3[CH2:15][C@H:14]([OH:16])[C@H:13]([CH2:17][OH:18])[CH2:12]3)[C:4]=2[N:5]=[CH:6][N:7]=1.N1C=CN=C1.[Si:24](Cl)([C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:26])[CH3:25]>CN(C=O)C>[NH2:1][C:2]1[C:3]2[CH:10]=[CH:9][N:8]([C@H:11]3[CH2:15][C@H:14]([OH:16])[C@H:13]([CH2:17][O:18][Si:24]([C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:26])[CH3:25])[CH2:12]3)[C:4]=2[N:5]=[CH:6][N:7]=1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 58944562HCID 58944562, compound

Product 1

HCID 58944550HCID 58944550, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (1S,2S,4R)-4-(4-amino-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-2-(hydroxymethyl)cyclopentanol (43.0 mg, 0.173 mmol) and imidazole (25.0 mg, 0.367 mmol) in dry DMF (2.00 mL) at 0° C. was added tert-butyldimethylsilyl chloride (29.0 mg, 0.192 mmol). The solution was stirred at rt for 2 h and concentrated in vacuo, the residue was dissolved in water and extracted with EtOAc. The combined organic extracts were dried over MgSO4, filtered and concentrated in vacuo to afford the title compound (50.8 mg, 81%), which was taken on without further purification. LC/MS: Rt=1.38 min, ES+ 364 (FA standard).

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionthe residue was dissolved in water
  3. extractionextracted with EtOAc
  4. dry with materialThe combined organic extracts were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7e0c3224403d4db693bee63f7db92287
Source dataset
uspto-grants-2012_06
Patent number
US08207177B2

Reaction notes

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